Wale’s friends turn to the street life in lieu of what seems like their only other option, getting a minimum wage job at McDonalds. Jay-Z rapped about this same dilemma on the “Get By” remix:

Picture me working McDonald’s
I’d rather pull a Mac on you
Sorry Ms. Jackson, but I’m packing

Wale puns on “chain” here as in the necklace, and in a more literal sense:

Harriet Tubman led more than 300 slaves to freedom by way of the Underground Railroad

Wale here talks about the cycles of poverty, with drug dependence and hopelessness in one generation often continuing into the next. Here, he puns on the myth of crack babies – the now-discredited idea that babies born to cocaine-addicted mothers faced severe disabilities

There are a lot more guns in D.C. since the Supreme Court struck down a city-wide gun ban in 2008

Rocky, as he likes to do, starts spitting some of that “Houston shit” – touting the virtues of purple drank, the combination of promethazine- and codeine-laced cough syrup with soda and/or pieces of Jolly Rancher candy. Purple drank was popularized by the late Houston rap pioneer DJ Screw and his clique, which he called the “Screwed Up Click”